Stereoselective synthesis of 1,2-amino alcohols by addition of organocuprate·BF3 complexes and organolithium reagents to an α-silyloxyaldimine derived from (S)-ethyl lactate

Tetrahedron

Volumn 52, Issue 41, 1996, Pages 13137-13144

  Ishimaru, Kaori ^a   Tsuru, Kazutaka ^a   Yabuta, Katsunori ^a   Wada, Makoto ^a   Yamamoto, Yohsuke ^a   Akiba, Kin Ya ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030271873     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00776-4     Document Type: Article

References (28)

1. 1) Ager, D.J.; Prakash, I.; Schaad, D.R. Chem. Rev. 1996, 96, 835. Cooke, J.W.B.; Davies, S.G.; Naylor, A. Tetrahedron 1993, 49, 7955. Donnelly, D.M.X.; Fitzpatrick, B.M.; O'Reilly B.A.; Finet, J.-P. Tetrahedron 1993, 49, 7967. Enders, D.; Reinhold, U. Angew. Chem. Int. Ed. Engl. 1995, 34, 1219. Deng, J.; Hamada, Y.; Shioiri, T. J. Am. Chem. Soc. 1995, 117, 7824. Gennari, C.; Pain, G.; Moresca, D. J. Org. Chem. 1995, 60, 6248.
2. 1) Ager, D.J.; Prakash, I.; Schaad, D.R. Chem. Rev. 1996, 96, 835. Cooke, J.W.B.; Davies, S.G.; Naylor, A. Tetrahedron 1993, 49, 7955. Donnelly, D.M.X.; Fitzpatrick, B.M.; O'Reilly B.A.; Finet, J.-P. Tetrahedron 1993, 49, 7967. Enders, D.; Reinhold, U. Angew. Chem. Int. Ed. Engl. 1995, 34, 1219. Deng, J.; Hamada, Y.; Shioiri, T. J. Am. Chem. Soc. 1995, 117, 7824. Gennari, C.; Pain, G.; Moresca, D. J. Org. Chem. 1995, 60, 6248.
3. 1) Ager, D.J.; Prakash, I.; Schaad, D.R. Chem. Rev. 1996, 96, 835. Cooke, J.W.B.; Davies, S.G.; Naylor, A. Tetrahedron 1993, 49, 7955. Donnelly, D.M.X.; Fitzpatrick, B.M.; O'Reilly B.A.; Finet, J.-P. Tetrahedron 1993, 49, 7967. Enders, D.; Reinhold, U. Angew. Chem. Int. Ed. Engl. 1995, 34, 1219. Deng, J.; Hamada, Y.; Shioiri, T. J. Am. Chem. Soc. 1995, 117, 7824. Gennari, C.; Pain, G.; Moresca, D. J. Org. Chem. 1995, 60, 6248.
4. 1) Ager, D.J.; Prakash, I.; Schaad, D.R. Chem. Rev. 1996, 96, 835. Cooke, J.W.B.; Davies, S.G.; Naylor, A. Tetrahedron 1993, 49, 7955. Donnelly, D.M.X.; Fitzpatrick, B.M.; O'Reilly B.A.; Finet, J.-P. Tetrahedron 1993, 49, 7967. Enders, D.; Reinhold, U. Angew. Chem. Int. Ed. Engl. 1995, 34, 1219. Deng, J.; Hamada, Y.; Shioiri, T. J. Am. Chem. Soc. 1995, 117, 7824. Gennari, C.; Pain, G.; Moresca, D. J. Org. Chem. 1995, 60, 6248.
5. 1) Ager, D.J.; Prakash, I.; Schaad, D.R. Chem. Rev. 1996, 96, 835. Cooke, J.W.B.; Davies, S.G.; Naylor, A. Tetrahedron 1993, 49, 7955. Donnelly, D.M.X.; Fitzpatrick, B.M.; O'Reilly B.A.; Finet, J.-P. Tetrahedron 1993, 49, 7967. Enders, D.; Reinhold, U. Angew. Chem. Int. Ed. Engl. 1995, 34, 1219. Deng, J.; Hamada, Y.; Shioiri, T. J. Am. Chem. Soc. 1995, 117, 7824. Gennari, C.; Pain, G.; Moresca, D. J. Org. Chem. 1995, 60, 6248.
6. 1) Ager, D.J.; Prakash, I.; Schaad, D.R. Chem. Rev. 1996, 96, 835. Cooke, J.W.B.; Davies, S.G.; Naylor, A. Tetrahedron 1993, 49, 7955. Donnelly, D.M.X.; Fitzpatrick, B.M.; O'Reilly B.A.; Finet, J.-P. Tetrahedron 1993, 49, 7967. Enders, D.; Reinhold, U. Angew. Chem. Int. Ed. Engl. 1995, 34, 1219. Deng, J.; Hamada, Y.; Shioiri, T. J. Am. Chem. Soc. 1995, 117, 7824. Gennari, C.; Pain, G.; Moresca, D. J. Org. Chem. 1995, 60, 6248.
7. 2) Boyle, P.H.; Davis, A.P.; Dempsey, K.J.; Hosken, G.D. Tetrahedron: Asymmetry 1995, 6, 2819. Davis, A.P.; Dempsey, K.J. Tetrahedron: Asymmetry 1995, 6, 2829.
8. 2) Boyle, P.H.; Davis, A.P.; Dempsey, K.J.; Hosken, G.D. Tetrahedron: Asymmetry 1995, 6, 2819. Davis, A.P.; Dempsey, K.J. Tetrahedron: Asymmetry 1995, 6, 2829.
9. 3) Blaser, H.-U. Chem. Rev. 1992, 92, 935.
10. 4) Bocoum, A.; Boga, C.; Savoia, D.; Umani-Ronchi, A. Tetrahedron Lett. 1991, 32, 1367. Volkmann, R. A.; Davis, J. T.; Meltz, C.N. J. Am. Chem. Soc. 1983, 105, 5946. Scully, F.E. J. Org. Chem. 1980, 45, 1515. Stork, G.; Dowd, S.R. J. Am. Chem. Soc. 1963, 85, 2178. Hosomi, A.; Araki, Y.; Sakurai, H. J. Am. Chem. Soc. 1982, 104, 2081.
11. 4) Bocoum, A.; Boga, C.; Savoia, D.; Umani-Ronchi, A. Tetrahedron Lett. 1991, 32, 1367. Volkmann, R. A.; Davis, J. T.; Meltz, C.N. J. Am. Chem. Soc. 1983, 105, 5946. Scully, F.E. J. Org. Chem. 1980, 45, 1515. Stork, G.; Dowd, S.R. J. Am. Chem. Soc. 1963, 85, 2178. Hosomi, A.; Araki, Y.; Sakurai, H. J. Am. Chem. Soc. 1982, 104, 2081.
12. 4) Bocoum, A.; Boga, C.; Savoia, D.; Umani-Ronchi, A. Tetrahedron Lett. 1991, 32, 1367. Volkmann, R. A.; Davis, J. T.; Meltz, C.N. J. Am. Chem. Soc. 1983, 105, 5946. Scully, F.E. J. Org. Chem. 1980, 45, 1515. Stork, G.; Dowd, S.R. J. Am. Chem. Soc. 1963, 85, 2178. Hosomi, A.; Araki, Y.; Sakurai, H. J. Am. Chem. Soc. 1982, 104, 2081.
13. 4) Bocoum, A.; Boga, C.; Savoia, D.; Umani-Ronchi, A. Tetrahedron Lett. 1991, 32, 1367. Volkmann, R. A.; Davis, J. T.; Meltz, C.N. J. Am. Chem. Soc. 1983, 105, 5946. Scully, F.E. J. Org. Chem. 1980, 45, 1515. Stork, G.; Dowd, S.R. J. Am. Chem. Soc. 1963, 85, 2178. Hosomi, A.; Araki, Y.; Sakurai, H. J. Am. Chem. Soc. 1982, 104, 2081.
14. 4) Bocoum, A.; Boga, C.; Savoia, D.; Umani-Ronchi, A. Tetrahedron Lett. 1991, 32, 1367. Volkmann, R. A.; Davis, J. T.; Meltz, C.N. J. Am. Chem. Soc. 1983, 105, 5946. Scully, F.E. J. Org. Chem. 1980, 45, 1515. Stork, G.; Dowd, S.R. J. Am. Chem. Soc. 1963, 85, 2178. Hosomi, A.; Araki, Y.; Sakurai, H. J. Am. Chem. Soc. 1982, 104, 2081.
15. 5) Wada, M.; Sakurai, Y.; Akiba, K.-y. Tetrahedron Lett. 1984, 25, 1079.
16. Wada, M.; Aiura, H.; Akiba, K.-y. Tetrahedron Lett. 1987, 28, 3377.
17. 6) Lipshutz, B.H.; Sengupta, S. Organic Reactions 1993, 41, 135.
18. 7) During the course of our study, addition of Grignard derived organocopper•BF3 complex to N-trimethylsilylimines was reported; Cainelli, G.; Giacomini, D.; Panunzio, M.; Zarantonello, P. Tetrahedron Lett. 1992, 33, 7783. They reported organolithium derived organocopper•BF3 complexes showed poor selectivities which are different from our results.
19. 8) Addition of Grignard and organolithium reagents to an α-benzyloxyimine appeared recently; Franz, T.; Hein, M.; Veith, U.; Jäger, V.; Peters, E.-M.; Peters, K.; von Schnering, H.G. Angew. Chem. Int. Ed. Engl. 1994, 33, 1298.
20. 9) (a) Zioudrou, C.; Churysochou, P. Tetrahedron 1977, 33, 2103.
21. (b) Fujita, M.; Hiyama, T. J. Am. Chem. Soc. 1984, 106, 4629.
22. 10) Gawley, R.E.; Hart, G.C.; Bartolotti, L.J. J. Org. Chem. 1989, 54, 175.
23. 11) Kende, A.S.; Liu, K.; Kaldor, I.; Dorey, G.; Koch, K. J. Am. Chem. Soc. 1995, 117, 8258.
24. 12) Yamamoto, Y. Angew. Chem. Int. Ed. Engl. 1986, 25, 947.
25. 13) Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968,15, 2199. Anh, N.T. Top. Curr. Chem. 1980, 88, 145.
26. 13) Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968,15, 2199. Anh, N.T. Top. Curr. Chem. 1980, 88, 145.
27. 14) Hirama, M.; Nishizaki, I.; Shigemoto, T.; Ito, S. J. Chem. Soc. Chem. Commun. 1986, 393.
28. 15) Coppens, P.; Hamilton, W. C. Acta Crystallogr. 1970, A26, 71.